Family-friendly holiday rentals in Wellington

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Wellington

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
The exterior of the cottage showcases blue siding and features a welcoming porch with bright yellow chairs. A black door with decorative glass invites guests into the home. The design reflects a blend of cottage charm and modern touches.
Home in Wellington
4.98 out of 5 average rating, 218 reviews

Little Blue Cottage: Perfect for families!

This little blue house is in the heart of Wellington. 5 min to The Drake, grocery, cafes, shops & market. Easy walk to the beach and trail for miles of biking, even past wineries! Newly renovated with a lovely kitchen & bathroom. This house has 2 bedrooms, (1 queen bed and 2twin beds). The home is sunny and has been designed with comfort in mind. Privacy & location make this a great base to explore PEC! Please note that July & August bookings are minimum 7 days with check in/out on Saturday

Guest favourite
A cozy unit features a well-equipped kitchenette, highlighted by modern cabinetry and a small refrigerator. A spacious bed is adorned with neutral tones and decorative pillows. A mirror reflects light, while a dining area with two chairs and a woven rug adds warmth to the space.
Flat in Belleville
4.93 out of 5 average rating, 159 reviews

Modern Boho Studio | Cozy Stay + Kitchenette

Nestled just 5 minutes north of the 401 highway at Belleville, or 20 minutes north of PEC, The Ashley is a charming oasis of modern comfort and convenience. A renovated gem boasts a sleek and contemporary design, ensuring a memorable stay in every single unit. Whether you're here for a golf getaway or to explore the local attractions, you'll find our motel to be the perfect starting point for your adventure. Book your stay with us and discover a world of relaxation, excitement, and golfing fun.

Top guest favourite
A well-appointed bedroom features a spacious bed with a quilted cover adorned with colorful patterns. A rustic wooden accent wall serves as a striking backdrop. Soft lighting is provided by two hanging lamps, and a small bedside table complements the decor.
Flat in Wellington
4.95 out of 5 average rating, 459 reviews

The Village Suites - THE VINEYARD

Beautiful 1 bedroom suite on Main Street, in the Heart of Wellington. Steps away The Drake Devonshire, East and Main Bistro and Midtown Brewery Across the street enjoy our local piano bar "The Stache". For great coffee and breakfast head to Enid Grace Cafe. Also, Ice cream and bike rentals just outside your door Head out for the afternoon to enjoy over 40 Wineries surrounding Wellington such as Hillier Estates , Sandbanks, Casa-Dea plus many more! A must see is our World famous Sandbanks Beach.

Top guest favourite
A bright eat-in kitchenette features a round wooden table surrounded by two upholstered chairs. Open shelving displays kitchen essentials, with plants adding a touch of greenery. Modern appliances, including a microwave and coffee maker, are neatly arranged along the counter.
Guest suite in Wellington
5 out of 5 average rating, 136 reviews

Wellington Guest Suite on Main!

Our 1928 Victorian-style home is on Main Street in Wellington! This offers the convenience of walking out your front door & enjoying our charming village by the water & all it has to offer. Our guest suite is a newly renovated 1 bdrm with lounge area, 1 bath & eat-in kitchenette if you wish to make breakfast/lunch. Enjoy morning coffee or before dinner cocktail on our deck outside the guest suite to take in the great vibe of Wellington & people enjoying this community. License #ST-2023-0009

Top guest favourite
The open-concept guest house interior features a spacious sleeping area with a large bed. Natural light enters through sliding glass doors and tall windows, illuminating warm wooden beams and light-colored walls. A cozy seating area with two chairs and a table is visible, complemented by decorative plants.
Guest house in Bloomfield
4.98 out of 5 average rating, 130 reviews

The Bloomfield Guest House

Are you looking for an awe-inspiring, peaceful, retreat-like setting for your visit to The County? Book this well-crafted private guest-house in charming Bloomfield, perfectly located between Wellington and Picton. The expansive farm-field view will instantly ground and settle your being. Every aspect of this luxury offering has been designed and built with integrity and care. We welcome you to embody a felt-sense of coming home. Follow us @thebloomfieldguesthouse Licence # ST-2022-0076

Top guest favourite
The spacious room features a large bed with crisp linens and a decorative throw. A cozy seating area includes a sofa and wooden table, while natural light illuminates the space through a nearby window. A tasteful arrangement of artwork enhances the welcoming environment.
Guest suite in Wellington
4.92 out of 5 average rating, 377 reviews

Walk to Drake, 20+ Hillier wineries, Rotary Beach!

Welcome to Prince Edward County! Our spacious 800sqft rental has you located within a 5 minute walk to downtown Wellington where you can enjoy amazing meals at the Drake Devonshire, Idle Wild, East & Main and El Condesa. You're a 20 minute bike ride from renowned wineries such as Norman Hardie, The Grange, Closson Chase and 20+ others. Finally, you're only a 20 minute drive from Sandbanks, an Ontario provincial park with three expansive sandy beaches on Lake Ontario. Enjoy County living!

Top guest favourite
A cozy living area features a rustic wood stove, complemented by two stylish chairs and a vibrant area rug. Large windows frame the serene view of Lake Ontario, enhancing the space's inviting ambiance.
Guest house in Wellington
4.98 out of 5 average rating, 274 reviews

Little Ben Prince Edward County

Little Ben's license allows 2 adults and one child age 10 and under. Located ten feet from Lake Ontario, in the heart of beautiful Wellington, Little Ben is a fully renovated 1 bedroom cottage in the centre of wine country. Little Ben offers a fully equipped kitchen, a dining area and a comfy living area with a wood stove. The true glory of Little Ben exists outside its walls--you are just a mere ten steps down to your own limestone beach on Lake Ontario! Licence Number ST-2019-0358

Superhost
A welcoming living area features sunlight streaming through large windows. Colorful seating includes a green armchair and an iconic yellow chair, complemented by a stylish side table. A houseplant adds a touch of greenery, and a message board is ready for personalized notes.
Flat in Picton
4.83 out of 5 average rating, 119 reviews

Funky studio Apt Full kitchen 5 min to Main St

Welcome to our renovated Mid Century Modern private studio apartment. Designed for comfort, functionality and convenience, featuring unique colorful furnishings offering you an alternative hotel stay. The apt is fully equipped for your comfortable stay, featuring a queen bed, full kitchen with new appliances, including a full size stove, microwave and fridge/freezer to accommodate your extended stay. You have your own full private bathroom with walk-in shower and in-suite laundry

Guest favourite
The studio features a spacious bed with an earthy-toned duvet, complemented by a wooden headboard. A cozy seating area with a vibrant yellow couch is visible in the background, alongside decorative wall elements and plants that add a touch of greenery.
Flat in Picton
4.9 out of 5 average rating, 218 reviews

Modern open concept farmhouse studio w/parking

Welcome to Unit #3 at the Picton Commons! Located on Main St. near historic Picton Harbour, this mid-century modern studio offers a stylish and cozy retreat for those looking to explore PEC. Our unit features a tastefully renovated interior, complete with a king sized bed, farmhouse kitchen, as well as a private outdoor patio and free street parking directly outside. Steps away from the county fairground and a short walk to the best restaurants and shops Picton has to offer.

Top guest favourite
The Hull House sits gracefully on a limestone shelf overlooking Lake Ontario. Lush greenery surrounds the home, complemented by a spacious lawn. A sunken deck with seating faces the water, providing an inviting outdoor space for relaxation. Grapevines can be seen in the distance.
Home in Prince Edward
4.98 out of 5 average rating, 218 reviews

The Hull House - Lake Ontario Waterfront w Sauna

Perched atop a picturesque limestone shelf on the shores of Lake Ontario, just 4 kilometres west of Wellington, is the Hull House. A thoughtfully curated County Lakehouse that boasts an infinite view of blue waters and ever changing skies. Ideally located at the centre of Prince Edward County’s web of vibrant restaurants and wineries, the Hull House offers 200 + feet of private lake frontage, 2 acres of land, a sauna and many luxuries for your well deserved vacation.

Guest favourite
A wooden deck overlooks a serene lakeside view, featuring two adirondack chairs positioned for relaxation. A circular table is set nearby, surrounded by greenery and the tranquil ambiance of the lake in the background.
Cottage in Prince Edward
4.88 out of 5 average rating, 112 reviews

Bright and Cheerful 2-bedroom, Lakefront Cottage

Lakefront cottage located in beautiful Prince Edward County. Great for 2 adults and 2 children. This adorable 2 bedroom cottage is on Consecon Lake, 5 minutes from the village of Consecon and close to beaches, wineries, Wellington and the 401. Enjoy the central location as you explore this beautiful region! More space available next door: https://www.airbnb.com/l/rW8ddIpQ

Top guest favourite
The exterior of a charming farmhouse features a light-colored facade and dark roof, framed by neatly trimmed shrubs and lush grass. A welcoming wooden door is flanked by glass panels, while a spacious porch is partially enclosed with large windows, inviting relaxation.
Home in Wellington
4.96 out of 5 average rating, 180 reviews

Our County Place

In the heart of Wellington, our updated 1880's farmhouse offers the best of the county. Bike to world-class vineyards, walk to the beach and great restaurants, or kick-back by a bonfire and count the stars. (July and August, weekly only Saturday to Saturday) Our County Place is a registered Short-term Accommodation in Prince Edward County (#ST-2019-0350)

Popular amenities for Wellington family-friendly rentals

When is the best time to visit Wellington?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$262 SGD$237 SGD$261 SGD$319 SGD$353 SGD$385 SGD$423 SGD$437 SGD$342 SGD$294 SGD$278 SGD$248 SGD
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Quick stats about holiday rentals that are family-friendly in Wellington

  • Total holiday rentals

    Explore 80 holiday rentals in Wellington

  • Nightly prices starting at

    Wellington holiday rentals start at $130 SGD per night before taxes and fees

  • Verified guest reviews

    Over 6,680 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    80 of Wellington holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wellington rentals

  • 4.9 Average rating

    Wellington stays are highly rated by guests – averaging 4.9 out of 5!